MINNELIDE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H25O10P.2Na
Molecular Weight	514.3705
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[Na+].CC(C)[C@]12O[C@H]1[C@@H]3O[C@]34[C@]5(O[C@H]5C[C@H]6C7=C(CC[C@]46C)C(=O)OC7)[C@@H]2OCOP([O-])([O-])=O

InChI

InChIKey=ZHBJMVNZRZUQEP-KIKMAQITSA-L

InChI=1S/C21H27O10P.2Na/c1-9(2)19-14(30-19)15-21(31-15)18(3)5-4-10-11(7-26-16(10)22)12(18)6-13-20(21,29-13)17(19)27-8-28-32(23,24)25;;/h9,12-15,17H,4-8H2,1-3H3,(H2,23,24,25);;/q;2*+1/p-2/t12-,13-,14-,15-,17+,18-,19-,20+,21+;;/m0../s1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C21H25O10P
Molecular Weight	468.391
Charge	-2
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT03117920 | https://clinicaltrials.gov/ct2/show/NCT01927965 | https://clinicaltrials.gov/ct2/show/NCT03760523 https://www.ncbi.nlm.nih.gov/pubmed/31109340 | https://www.ncbi.nlm.nih.gov/pubmed/28543919https://www.ncbi.nlm.nih.gov/pubmed/27222828 | https://www.ncbi.nlm.nih.gov/pubmed/25400429https://www.ncbi.nlm.nih.gov/pubmed/30599444 | https://adisinsight.springer.com/drugs/800016015 | https://www.ncbi.nlm.nih.gov/pubmed/19251409/ | https://www.ncbi.nlm.nih.gov/pubmed/21255694
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27921038 https://www.drugs.com/npp/thunder-god-vine.html

Omtriptolide (previously known as PG490-88 or F60008), an immunosuppressant that has been shown to be the safe and potent antitumor agent and it has been approved entry into Phase I clinical trial for the treatment of prostate cancer in the USA. In addition, the drug is participating in phase I clinical trial for the treatment of myeloid leukemia. Experiments on animals have shown omtriptolide was highly effective in the prevention of murine graft-versus-host disease (GVHD). The immunosuppressive effect of the drug was mediated by inhibition of alloreactive T cell expansion through interleukin-2 production. However, this study was discontinued. Recently published article has shown omtriptolide possesses the potential as a prophylactic agent to prevent ischemia/reperfusion (I/R)-induced lung injury.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A2 73 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26874845	Inhibitor 8504	14.18 µM [IC50]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26874845	Inhibitor 8504	8.36 µM [IC50]
NF-kappa B signaling pathway 87 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26531258	Inhibitor 8504
HuCCT1, human cholangiocarcinoma 5 Target ID: HuCCT1, human cholangiocarcinoma Sources: https://www.ncbi.nlm.nih.gov/pubmed/24742042	Inhibitor 8504	12.6 nM [IC50]
beta-amyloid formation 6 Target ID: GO:0034205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23126204	Inhibitor 8504	30.0 pM [IC50]
Proteinase-activated receptor 2 7 Target ID: CHEMBL5963 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23895492	Antagonist 2849	14.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Autosomal dominant polycystic kidney disease 7 Sources: https://clinicaltrials.gov/ct2/show/NCT02115659	Primary	Phase III 665	Unknown Approved Use Unknown
HIV-1 infection 156 Sources: https://clinicaltrials.gov/ct2/show/NCT01817283 https://clinicaltrials.gov/ct2/show/NCT02219672	Primary	Phase III 665	Unknown Approved Use Unknown
Crohn's disease 64 Sources: https://clinicaltrials.gov/ct2/show/NCT02044952	Primary	Phase III 665	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946	substrate 1193 inhibitor 2438	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 BCRP 910 CYP2C8 1057 CYP1A2 2153 P-gp 1741 CYP2A6 879 CYP2E1 1060	CYP2C8 810 CYP2E1 729 CYP1A2 1197 CYP2A6 626 P-gp 2052 CYP2C19 1119 CYP2B6 776 OCT2 434

Drug as perpetrator

Target	Modality	Activity
CYP2A6 911	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26874845/	no [Inhibition 100 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26874845/	no [Inhibition 100 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26874845/	no [Inhibition 100 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26874845/	no [Inhibition 100 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26874845/	no [Inhibition 100 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26874845/	no [Inhibition 50 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26874845/	no [Inhibition 50 uM]
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1325#sid=26719814	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26874845/	yes [IC50 14.18 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26874845/	yes [IC50 8.36 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18982531/	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18982531/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18982531/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18982531/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18982531/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18982531/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18982531/	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18982531/	yes
OCT2 434	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31644961/	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30112986/	yes
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30112986/	yes	yes (co-administration study) Comment: Grapefruit juice increased AUC and Cmax by 153% and 141% Sources: https://pubmed.ncbi.nlm.nih.gov/30112986/

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0036BN	https://www.1pchem.com/search?query=1P0036BN
A2B Chem	AB47363	http://a2bchem.com/prod/AB47363
AChemBlock	10401	http://www.achemblock.com/catalogsearch/result/?q=10401
AK Scientific	S493	https://aksci.com/item_detail.php?cat=S493
Ambeed	A550309	http://www.ambeed.com/search/Search.html?keyword=A550309
ApexBio Technology	A3891	https://www.apexbt.com/catalogsearch/result/?q=A3891
AstaTech	44358	http://astatechinc.com/CPSResult.php?CRNO=44358
Biopurify Phytochemicals	BP1411	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP1411&searchhtmp=simplesearch&t=1
BioSynth	Q-100450	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100450
BLD Pharm	BD9097	http://www.bldpharm.com/search/Search.html?keyword=BD9097
BOC Sciences	38748-32-2	http://www.bocsci.com/description.asp?cas=38748-32-2
Cayman Chemical	11973	http://www.caymanchem.com/app/template/Product.vm/catalog/11973
Chem-Impex International	30404	http://www.chemimpex.com/category/search/30404/2?filter=&search=30404&type=q&keywordoption=ANY&cid=2&fltrdesc=
Chem Scene	CS-0286	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0286
Chemodex	T0237	http://www.chemodex.com/products/T0237
ChemShuttle	151843	https://www.chemshuttle.com/catalogsearch/result/?q=151843
eMolecules	25686240	https://orderbb.emolecules.com/search/#?query=25686240
eMolecules	29781300	https://orderbb.emolecules.com/search/#?query=29781300
eMolecules	300613932	https://orderbb.emolecules.com/search/#?query=300613932
eNovation Chemicals	D480547	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D480547&searchbtn.x=0&searchbtn.y=0
Lab Network	LN01293795	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01293795
Lab Network	LN02196201	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN02196201
Lab Seeker	SC-14019	http://www.labseeker.com/search.php?keywords=SC-14019&category=0
LabSeeker	SC-14019	http://www.labseeker.com/search.php?keywords=SC-14019&category=0
mcule	MCULE-3581898493	https://mcule.com/MCULE-3581898493/
mcule	MCULE-5702185362	https://mcule.com/MCULE-5702185362/
MedChem Express	HY-32735	https://www.medchemexpress.com/search.html?q=HY-32735&ft=&fa=&fp=
Molnova	M14333	https://www.molnova.com/en/serch-list.html?keywords=M14333
MolPort	MolPort-016-638-463	https://www.molport.com/shop/molecule-link/MolPort-016-638-463
PI Chemicals	PI-28474	http://www.pipharm.com/catalog_products/PI-28474.html
Ryan Scientific	Cyclopamine	https://ryansci.com/products?q=Cyclopamine&list_q=&search_type=exact
Selleck Chemicals	S3604	http://www.selleckchem.com/search.html?searchDTO.searchParam=S3604
ShangHai Biochempartner	BCP000185	http://www.biochempartner.com/search_BCP000185
TargetMol	T2179	https://www.targetmol.com/search?keyword=T2179
Tetrahedron	TS59472	http://www.thsci.com/search.do?q=TS59472
Tocris	3253	https://www.tocris.com/search.php?Type=QuickSearch&Value=3253
Toronto Research Chemicals	T815600	https://www.trc-canada.com/product-detail/?CatNum=T815600
W&J PharmaChem	50C186866	http://wjpharmachem.com/new/searcht.php?keyword=50C186866

PubMed

Title	Date	PubMed
Pre-clinical evaluation of Minnelide as a therapy for acute myeloid leukemia.	2019-05-20	31109340
PG490-88, a derivative of triptolide, suppresses ischemia/reperfusion-induced lung damage by maintaining tight junction barriers and targeting multiple signaling pathways.	2019-03	30599444
Downregulation of Sp1 by Minnelide leads to decrease in HSP70 and decrease in tumor burden of gastric cancer.	2017	28192510
Suppression of the migration and invasion is mediated by triptolide in B16F10 mouse melanoma cells through the NF-kappaB-dependent pathway.	2016-12	26420756
Protection of Quercetin against Triptolide-induced apoptosis by suppressing oxidative stress in rat Leydig cells.	2015-10-05	26277538
Triptolide disrupts fatty acids and peroxisome proliferator-activated receptor (PPAR) levels in male mice testes followed by testicular injury: A GC-MS based metabolomics study.	2015-10-02	26219505
Inhibition of P-glycoprotein Gene Expression and Function Enhances Triptolide-induced Hepatotoxicity in Mice.	2015-07-02	26134275
Triptolide-induced oxidative stress involved with Nrf2 contribute to cardiomyocyte apoptosis through mitochondrial dependent pathways.	2014-11-04	25169008
Interleukin-17 mediates triptolide-induced liver injury in mice.	2014-09	24949944
Establishment of hypoxia induction in an in vivo animal replacement model for experimental evaluation of pancreatic cancer.	2014-07	24842335
Gene expression profiling and pathway analysis of hepatotoxicity induced by triptolide in Wistar rats.	2013-08	23639586
Minnelide: a novel therapeutic that promotes apoptosis in non-small cell lung carcinoma in vivo.	2013	24143232
Role of Nrf2 in protection against triptolide-induced toxicity in rat kidney cells.	2012-09-03	22820427
Effect of triptolide on progesterone production from cultured rat granulosa cells.	2012-06	22592319
Triptolide down-regulates COX-2 expression and PGE2 release by suppressing the activity of NF-κB and MAP kinases in lipopolysaccharide-treated PC12 cells.	2012-03	21717513
Cytotoxicity of Triptolide and Triptolide loaded polymeric micelles in vitro.	2011-12	21640813
Knockout of hepatic P450 reductase aggravates triptolide-induced toxicity.	2011-08-10	21596114
Physio-pathological parameters affect the activation of inflammatory pathways by deoxynivalenol in Caco-2 cells.	2010-10	20633634
Identification of triptolide, a natural diterpenoid compound, as an inhibitor of lung inflammation.	2010-06	20348278
Sex differences in subacute toxicity and hepatic microsomal metabolism of triptolide in rats.	2010-04-30	20223271
Effects of cytochrome P4503A inducer dexamethasone on the metabolism and toxicity of triptolide in rat.	2010-02-01	19879934
Triptolide alters histone H3K9 and H3K27 methylation state and induces G0/G1 arrest and caspase-dependent apoptosis in multiple myeloma in vitro.	2010-01-12	19879315
Phase I dose-escalation study of F60008, a novel apoptosis inducer, in patients with advanced solid tumours.	2009-07	19251409
Heat shock protein 72 protects kidney proximal tubule cells from injury induced by triptolide by means of activation of the MEK/ERK pathway.	2009-06-24	19546256
Caspase 3 is involved in the apoptosis induced by triptolide in HK-2 cells.	2009-06	19233258
Interleukin-6-independent expression of glucocorticoid receptor is upregulated by triptolide in multiple myeloma.	2009-05	19330649
Triptolide cooperates with chemotherapy to induce apoptosis in acute myeloid leukemia cells.	2008-12	18922616
Triptolide protects podocytes from puromycin aminonucleoside induced injury in vivo and in vitro.	2008-09	18509322
Upregulation of ICAM-1 expression in bronchial epithelial cells by airway secretions in bronchiectasis.	2008-02	17931847
Differential expression and oxidation of MKP-1 modulates TNF-alpha gene expression.	2007-09	17507666
Triptolide upregulates NGF synthesis in rat astrocyte cultures.	2007-07	17401680
Triptolide binds covalently to a 90 kDa nuclear protein. Role of epoxides in binding and activity.	2007	17678712
Dipyridamole activation of mitogen-activated protein kinase phosphatase-1 mediates inhibition of lipopolysaccharide-induced cyclooxygenase-2 expression in RAW 264.7 cells.	2006-07-17	16765938
[Study of triptolide-induced apoptosis in MUTZ-1 cells and its allied mechanism].	2005-06	15972136
Triptolide suppresses CD80 and CD86 expressions and IL-12 production in THP-1 cells.	2005-02	15663903
Mechanisms of tolerance induced by PG490-88 in a bone marrow transplantation model.	2002-01-15	11792990
PG490-88, a derivative of triptolide, blocks bleomycin-induced lung fibrosis.	2001-03	11238047

Patents

Sample Use Guides

In Vivo Use Guide

Minnelide will be administered at the dose of 0.67 mg/m2 as a 30 min infusion intravenously daily on days 1-21 of each cycle followed by a 7 day rest period (days 22-28)

Route of Administration: Intravenous

In Vitro Use Guide

The A549/Taxol cells were treated with different concentrationsof Triptolide (0.03, 0.3 or 3 uM/l) for 2, 4, 6 and 12 h. On exposure to 3 uM Triptolide for 2, 4, 6 and 12 h, the extent of cell apoptosis observed markedly increased. The inhibitory effect reached a maximum with 3 uM Triptolide at the 12 h time point (cell apoptotic rate, 65.33%), whereas the apoptotic rate of the control group was 7.23% at 12 h.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:36:53 GMT 2025` Edited by `admin` on `Mon Mar 31 22:36:53 GMT 2025`
Record UNII	1CIV2UMO40
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

14-O-PHOSPHONOOXYMETHYLTRIPTOLIDE DISODIUM SALT

Preferred Name

English

MINNELIDE

Common Name

English

TRISOXIRENO(4B,5:6,7:8A,9)PHENANTHRO(1,2-C)FURAN-1(3H)-ONE, 3B,4,4A,6,6A,7A,7B,8B,9,10-DECAHYDRO-8B-METHYL-6A-(1-METHYLETHYL)-6-((PHOSPHONOOXY)METHOXY)-, SODIUM SALT (1:2), (3BS,4AS,5AR,6R,6AS,7AS,7BS,8AS,8BS)-

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

388512